


Money and Misunderstandings

by dickspeightjrs



Category: Supernatural
Genre: Alternate Universe, Angst, Confused Dean Winchester, First Kiss, Fluff, Fluff and Angst, Law Student Sam Winchester, Lawyer Castiel (Supernatural), Lawyer Sam Winchester, M/M, Misunderstandings, Office Party, Past Castiel/Bart, Rich Castiel (Supernatural), Sam Winchester Ships Castiel/Dean Winchester, Strangers to Lovers, Supportive Castiel (Supernatural), Teacher Dean Winchester
Language: English
Status: Completed
Published: 2020-08-26
Updated: 2020-08-26
Packaged: 2021-03-07 02:27:16
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,018
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26129521
Author URL: https://archiveofourown.org/users/dickspeightjrs/pseuds/dickspeightjrs
Summary: Dean pulled at his tie again. He could swear they were designed originally as a way to torture people to death.Dean is Sam's plus one to his first ever party at the law firm he'd just started interning at. Now, Sam might be able to fit in with these snooty rich assholes, but that didn't mean Dean had to.
Relationships: Castiel & Sam Winchester, Castiel/Dean Winchester, Dean Winchester & Sam Winchester
Comments: 21
Kudos: 241





	Money and Misunderstandings

Dean pulled at his tie again. He could swear they were designed originally as a way to torture people to death.

Sam turned to see his brother fiddling with the knot. “Dude, stop it. The party has barely started, you can’t take your tie off yet.” He slapped Dean’s hand away. 

Dean grumbled. “Fine. I’ll keep it on. But I ain’t gonna act like I’m happy about it.” 

Sam just rolled his eyes in response.

It was looks like the bitch-face Sam was giving him that made Dean almost regret being proud as hell of his kid brother. 

Sam had just graduated from law school and managed to get an internship at the extremely prestigious Novak & Sons. Dean knew that the company must be a big deal because it had recently been splashed across the news. 

Apparently, the super old guy who owned the law firm had bitten the dust and left the whole thing to one of his sons. Dean couldn’t see the big deal about it all but Sam had been glued to the news the week that it all went down. 

Regardless, Sam was now an intern (though an unpaid one so Dean still helped him out with rent and bills), which meant he got invited to swanky parties thrown by the firm any time they sealed a major deal with another supposedly big deal client. 

Sam might be able to fit in with these snooty bastards, but Dean couldn’t. This wasn’t even a damn party. Just a bunch of rich people standing around chortling at each other and having conversations about the newest yacht they’d bought. 

Dean was interrupted in his grumblings by a guy walking up to him and Sam. 

“Winchester, isn’t it?” The guy asked Sam, obnoxiously. 

Dean bristled. This guy didn’t even know Sam’s name. Douchebag. 

“Yes, sir, it’s Sam.” Sam stuck out his hand for the man to shake. The man accepted, giving it a sharp shake. 

Then he turned his hard gaze to Dean. 

“And who is this?” The man said with a subtle sneer. 

“Oh, this is my brother, Dean Winchester. Dean, this is my boss, Michael Novak.” Sam introduced them. 

Ah! The ultimate douchebag. 

Neither man offered a hand to shake. They’d sussed each other already. 

“And what is it you do Dean?”  _ Because you certainly don’t belong here.  _

“I’m a kindergarten teacher.” Dean said, proudly 

Michael’s face soured further (if that was even possible). 

“Don’t they say that teaching kindergarten is like glorified babysitting?” Michael chortled. 

Dean’s eyes narrowed. This guy was already skating on thin fucking ice. And that ice just cracked. 

“Listen here, asshole.” Dean pointed a finger at the suited bastard. He could see Sam cringe and look at the floor next to him. But nothing would stop him now. “My kids are awesome. I’m  _ teaching _ them to be even more awesome adults when they’re older. I just hope none of them turn into jumped up douchebags like you.”

“Dean!” Sam despaired. 

“Sorry, Sam.” Dean mumbled. But he wasn’t sorry. Not really. He was only sorry that he’d embarrassed his brother. He would never apologise for defending his choice of career. 

Dean chanced a glance at Michael. If the dude was a cartoon, he’d probably have steam coming out of his ears right about now. 

“I’m going to the bar.” Dean murmured, leaving Sam to apologise on his brother’s behalf. 

Dean hoped there wouldn’t be consequences for Sam after his outburst. He just hated it when people looked down on other people for their jobs. Basic respect for others was something he prioritises with his kindergarteners. It was a shame that some adults couldn’t seem to grasp the concept. 

He walked through the crowd of guests like a storm cloud towards the bar. 

Luckily, it seemed most of the attendees were relying on the waiters for their drink orders meaning the bar was empty save for the bartender. Dean slumped onto one of the stools. 

“What’re you after, Brother?” The guy asked as he made his way over to Dean. 

“Whatever isn’t that fancy shit everyone else sees to be having.” 

The bartender, Benny his name tag read, laughed a deep, rich laugh. “I feel that. How’s a good, smooth whiskey sound?”

“Finally, someone talking my language.” Dean smiled. 

Benny passed him over a tumbler of gorgeous brown liquid. 

Dean lifted it in silent cheers and downed it in one go, sucking his lips at the sharp burn it sent down his throat. “Another one where that came from, dude.” Dean slid the glass across the bar top back towards Benny. 

“You sure, Brother?” Benny questioned. 

“Sure as shit. I gotta get through this night somehow.” Dean mumbled. 

“It can’t be that bad, can it?” A voice that wasn’t Benny’s (or Sam’s for that matter) appeared from Dean’s right. 

Dean turned his head to find a dude around his age looking back at him with distinctive blue eyes. 

The guy had on a suit and tie much like that other people in the room. But, the tie was loosened and curled backwards towards the end. His top button was undone and his trenchcoat that blanketed the whole outfit seemed as though it was barely hanging on to his shoulders. 

How come this guy could come dressed like that but Dean couldn't loosen the tie that had been strangling him for two hours already. (The dude looked like he’d just had seven minutes in heaven with someone in the cleaning cupboard for god’s sake!)

Dean was snapped out of his judgement of the guy in front of him by Benny placing a fresh glass of whiskey on the counter. The bartenders gave him a wink and looked slyly over to the trenchcoat guy still standing, leaning against the bar. 

What was Benny trying to say? 

Dean didn’t have long to think it over as the bartender moved away to collect dirty glasses at the other end of the bar, leaving Dean and the trenchcoat guy alone. 

“So,” Trenchcoat Guy continued, perching himself on the seat next to Dean, “what are you doing here if this evening is so torturous to you?” The words were said, not with bitter condescension like Michael might have asked, but, it seemed, with genuine interest. 

Alright, Dean could play ball. Plus, this guy was  _ hot _ . Dean would be thinking of a flirtatious answer if he wasn’t conscious of embarrassing Sam again by hitting on someone who is probably one of his co-workers.

“I’m here with my brother, Sam.” Dean explained. “He’s just started as an intern here. Wouldn’t kill the bastards to pay him though, he works harder than any kid I know.” 

Dean winced. He has gotta stop insulting the people Sam works with or  _ for _ . 

“And I take it, this isn’t your usual environment to socialise in?” Trenchcoat Guy enquired. 

Dean huffed a laugh. “You could say that. Turns out I don’t so much enjoy being looked down on for my job, no matter how much I might love my brother.” 

Trenchcoat Guy frowned. “What happened?”

“Some dude called Michael made a dick comment about me being a kindergarten teacher. Told him exactly what I thought about his opinion and embarrassed my brother in the process. So I sought refuge at the bar.” 

Blue eyes darkened. “That’s appalling! I’m sorry that happened.” Trenchcoat Guy placed an earnest but comforting hand on Dean’s. “Being a teacher is incredibly admirable. You’re helping to shape and guide future members of society.” He assured. “There’s nothing more noble than that. Definitely not a lawyer who seems to see the money before the client.” 

Where had this guy come from? He seemed a little weird and dorky but also genuine and caring. 

Dean shrugged off the compliment. Just because he wasn’t okay with people disrespecting his job, didn’t mean he was comfortable being showered with praise and kind words. 

Instead, Dean flagged down Benny and asked for a beer, looking to Trenchcoat Guy to silently ask if he’d like one too. Trenchcoat Guy nodded. 

The two men kept eye contact as they took the first sips of their beers. Dean’s eyes fell to the way the guy’s lips shaped around the lip of the bottle. He flicked his eyes up again to find the guy had seen the movement. He knew exactly what he was doing to Dean, if the way he slowly licked lingering droplets of beer from his bottom lip was anything to go by. 

Any other day, any other time and Dean would have jumped at the chance to, well, jump this guy. But, he wouldn't do that to Sam. 

Instead, he cursed the fates for sending him this awesome guy at exactly the wrong time. Taking another sip of his beer, he moved to get up from his seat. He’d better go find Sam and check he hadn’t ruined his brother’s position in the company. 

He was about to open his mouth to bid the beautiful stranger goodbye when the guy’s eyes left Dean’s and locked onto something over Dean’s shoulder. The blood seemed to drain from his face. Frantic blue eyes snapped back to Dean’s.

“Kiss me.”

“What?” Dean asked, confused at the turn this had taken. He could feel his resolve slipping. Sam’s reputation be damned. 

The guy didn’t answer. 

Suddenly, his hand was on Dean’s cheek and he was placing a deep kiss on Dean’s lips. 

Dean had no idea what was going on but his night had improved dramatically in the last three seconds so he definitely wasn’t going to complain. He placed a hand on the guy’s waist, pulling him in closer to his own body. 

After a few heated moments, the guy pulled away. Though Dean kept the hand on his waist so he couldn’t move far. He wasn’t letting him go any time soon, that was for sure. 

“I’m sorry.” Trenchcoat Guy panted, chest rising to gulp down air that he’d been deprived of. “My assbutt of an ex was coming towards us.” He tried to step back out of Dean’s embrace. 

But Dean held his grip firm. 

“No need to apologise, dude.” Dean assured. 

Looking into the guy’s eyes, feeling his moving chest against his own, Dean could feel his will power slipping. 

_Screw it._

Dean pressed his forehead against the other man’s. “Stop me if you don’t want this.” He whispered before he placed his lips over the other man’s.

The kiss was deepened instantly. By who Dean wasn’t sure but at this point, he really didn’t care. 

Dean allowed himself to be manhandled against the bar, never breaking the passionate connection he had with this wonderful stranger. 

As if the guy could read his mind he softened the kiss to whisper briefly against Dean’s lips. “I’m Castiel, by the way.”

Dean’s brain was so preoccupied that he could barely stutter out his own name in return. 

“Hmm.” Castiel hummed against Dean’s lips. “I don’t want to be presumptuous, Dean. But I’d very much like it if you took me home. Right now.” 

They broke apart and Dean looked into Castiel’s eyes. The calm blue from before had been replaced with seductive black. 

Yep. This was definitely happening. 

“Let’s go.” Dean grabbed Castiel’s hand to drag him towards the exit. 

But Castiel stopped him. 

“What about your brother?”

Shit. Trust his downstairs brain to throw logic out the window and forget about his brother. 

But he dreaded seeing the look of disappointment on Sam’s face when he told him where he was going. And who with. 

“Don’t worry, Brother.” Benny’s voice spoke up from the bar. “I’ll find him and let know you’ve gone home.” 

Dean shot Benny a grateful look. “Thanks, man.” He tried not to weirded out that Benny had seen what had just gone down. 

He once again grabbed Castiel’s hand and tugged him towards the nearest exit. 

Once outside, Dean hailed a taxi. He would have loved to have shown Castiel his beautiful 67 Impala but he’d had a couple of drinks and there was no way he was going to risk driving home. Plus, even without the drinks, he wasn’t sure he’d be able to keep his hands to himself long enough to get back to his. 

As soon as they made it through Dean’s front door, he sobered slightly. As respectful and understanding as Castiel had been earlier, he was clearly used to the finer things in life if he was at the firm party. Dean and Sam’s apartment was a far cry from that. 

“It’s not much…” Dean explained. 

Castiel turned from where he’d been doing a quick scan of the main room to lock eyes with Dean. “The only thing I’m concerned with right now is where your bed is.”

Dean could only point towards the corridor leading to his room. 

Castiel gave Dean a dark look and pulled him along by his tie. Maybe ties weren’t so bad after all. 

* * *

The next morning, Dean awoke to the feel of bare skin against his own. 

The body on top of his shifted and he could feel a rumble travel up through it. 

“Good morning, Dean.” Castiel hummed. 

“Mornin’, Sunshine.” Dean sighed, nuzzling into Castiel’s dark hair and placing a kiss against his temple. 

Dean was about to suggest breakfast when he sensed the stomping moose steps of Sam coming down the corridor outside his room. 

“I don’t care if you’re hungover, I’m shouting at-” Sam stormed into the room. But he was cut off by the sight in front of him.

Dean cringed. Benny obviously hadn’t told Sam everything when they’d left last night. 

“Oh my god! Mr Novak!” Sam snapped himself back to reality. 

Dean turned to look at Castiel.  _ Mr Novak? _ Was Castiel one of the stuck up sons of bitches sitting on a heck ton of money and not giving any of it to hard working interns like Sam? 

“Hello, Samuel.” Castiel greeted, lifting himself to sit against the headboard. “You can call me Castiel. I feel as though we’ve moved past the normal professional relationship now.” 

“Okay, Castiel.” Sam was clearly still in shock. “I’m just going to leave now.” He cleared his throat awkwardly and then ducked out of the room, closing the door softly behind him. 

Dean turned again to Castiel. “Okay, what just happened?” He asked, completely confused as hell. 

Castiel placed a hand on Dean’s. “I’ll explain everything but I think you need to go and make sure your brother is okay.” 

Dean was unsure. He didn’t want to just leave Castiel in his bed alone. 

“Go, Dean. I’ll wait here for you.” Castiel said, sensing Dean’s apprehension. 

“Okay.” Dean submitted, quickly pecking Castiel on the lips before getting up from the bed, throwing on some boxers and leaving the room. 

It wasn't until he was closing the bedroom door behind him that Dean realised he’d just kissed Castiel goodbye like they were boyfriends or something. 

Way to go, Dean. Scare the dude off before anything had properly started. 

Anyway, one problem at a time, he thought as he rounded the corner to find Sam pacing the length of the living room. 

“So…” Dean began, awkwardly. 

“I can’t believe you, Dean.” Sam said, angrily. “Did you not think of my career at all? Of all the people to go home with at that party, you went home with my boss?” 

Hang on..

“Boss?” Dean asked, “I thought that Michael dude was your boss?!” Dean said, confused as hell. 

Sam ran his hands through his hair in a frustrated manner. “I’m an intern, Dean. Practically everyone in the damn company is my boss. And Castiel? He’s  _ the _ boss.”

Dean paled. “What?”

Sam sighed. “He runs the whole damn thing! Didn’t you see the news a couple months ago? His dad died and left the whole firm solely to Castiel. It created a big stink because his brothers, including  _ Michael _ Novak, didn’t get a look in. They’ve been contesting the will for months now.”

Dean slumped onto the couch. He couldn’t believe it. Castiel had lied to him? Well, maybe not lied, just didn’t tell the whole truth. 

Sam saw Dean's mood suddenly turn and frowned. “You really didn’t know?” 

Dean silently shook his head. 

“I’m sure he has his reasons for not saying anything.” Sam tried to reassure his brother. 

Dean waved it off. “Don’t worry about it.” He said. “Yeah, I really like the guy, but once he realises who he shacked up with, he’s not gonna hang around.” He shrugged, accepting the situation for what it was. 

There was no way someone like Castiel, with that amount of wealth and riches, would be interested when he understood that Dean was a grown man who still lived with his little because they couldn’t afford much else right now. 

“Why don’t you let him decide that for himself?” Sam asked, pulling Dean from his negative thoughts. “All I know is, I’ve only met Castiel a handful of times but he’s only one of the Novak brothers that has ever tried to even learn my name.” 

Dean was torn. This was such a big thing for Castiel to neglect to mention. 

“Man, I don’t know. This only started because he was hiding from an ex at the party.” Dean explained. “And now I say it out loud, it sounds like a lie. God, I’m so stupid.” He dropped his head into his hands. 

“Damnit, Dean!” Don’t you ever watch anything on TV other than Doctor Sexy?” 

Huh? Dean shot his brother a confused squint. 

Sam shook his head in exasperation. “Even before their dad dying and the inheritance fiasco, the Novak brothers have always been sort of minor celebrities - comes with the money I guess.” Sam explained. “All I know is that he did have what the media called a ‘messy break up’ with a guy who worked for the company. And he was definitely at the party last night.” 

Dean sighed. He didn’t know what to think. 

“Look, Dean. You clearly like this guy already. He’s literally in your room waiting for you. Go talk to him.” 

Dean nodded and stood up, taking a determined breath. 

Sam gave him a supportive pat on the back. 

Just before he left the room, Dean turned back to his brother. “Are we good?”

Sam smiled. “Yeah, man, we’re good.”

Dean nodded and left. 

When he re-entered his room, Castiel was still sitting in Dean’s bed, picking at a thread in the covers. He looked up at the sound of the door clicking shut. 

“How did it go?” Castiel asked, patting the space next to himself, silently asking Dean to join him again. 

Dean sat on the bed, but he didn’t get back under the covers next to Castiel. He still wasn’t sure what to do. “It’s okay. We smoothed everything out.” Dean nodded. “Found out some stuff about you though.”

Castiel nodded in understanding. 

“Why didn’t you tell me you were the boss? My brother’s boss?!” Dean asked, pleading for an explanation. 

“I wanted to come up to you. I’d already seen you from across the room earlier and when I finally gathered the courage to come up to you, you were complaining about my party and clearly had no idea who I was.” Castiel explained. 

Dean flushed. “Sorry about that.”

“Don’t be sorry, Dean.” Castiel reached over to take Dean’s hand in both of his. “It was refreshing. With everything that has been going on recently, it was nice to have a break from that. And then my ex-boyfriend was coming towards us. And, well, you know the rest…” Castiel trailed off. 

“The douchebag who everyone seems to know about except me.” Dean added. “He sounds like a son of a bitch.” 

Castiel hummed in agreement. “That’s an understatement.” He muttered. “I found out Bart was sleeping with someone else a few months ago and I ended it immediately.” Castiel paused at Dean’s whispered ‘bastard’. “However, when my father died, he tried crawling back. He was probably after my new wealth and position in the company. I, of course, rejected him. But, Bart is the kind of person who doesn’t take no for an answer.” 

Dean scowled. He may have only just found out the diner details, but he wouldn’t hesitate to punch that dick in the face if he ever saw him. 

Taking in Castiel’s downtrodden look, Dean sighed. “I understand all of that Cas. But you heard me last night. You run the show and you seem like a decent guy but how can you have hard working interns like Sam and not pay them a cent? While you sit on a literal throne of money?” 

Dean looked down at his lap. He wasn’t sure he was going to like whatever Castiel had to say. 

“Dean,” Castiel lifted Dean’s chin to make the man look at him, “I completely agree with everything you said. That’s one of the reasons my father left everything to me.” Castiel explained. “He knew I had new ideas for the company. He knew it was only a matter of time before he had to hand it over to his sons. So he left it all to me on the sole condition that I go ahead with the changes that I wanted to implement.” 

Dean let out a breath and smiled. Okay, this sounded good. “What, uh, kinda stuff are you changing?” 

“Firstly, we’re going to be taking on a lot more pro bono cases. We  _ are _ sitting on a throne of money, as you say,” Dean blushed, “and it’s time we actually did something good with it.” 

Dean nodded. Now Castiel mentioned it, he remembered Sam saying something about that when he’d first joined Novak & Sons.

“And,” Castiel continued, “though it hasn’t been announced to the public or even the employees themselves, interns will be getting a competitive rate of pay. You’re right. They do work hard for us and they deserve to be properly credited for it.” 

Dean certainly hadn’t expected that. He’d expected Cas to say that it was out of his hands, or just simply that’s how things worked there. 

“Now, can you please say something? I’m worried I’ve ruined this before it could even begin.” Castiel asked, shyly.

Dean smiled softly. “As long as you don’t mind slumming it with someone like me, I only have one more question.” Castiel nodded. 

“Can I kiss you?”

Dean would give anything to never see that smile leave Cas’ face. 

Instead of answering, Castiel pulled Dean towards him by the shoulder. The smile didn’t leave his face as Dean pressed a long, sweet kiss to his lips. 

“I hope you’re ready,” Castiel said later after they’d parted for breath, “making out with the boss last night would have made quite a spectacle.” 

Dean made a noise of indifference just as Sam shouted from the living room. “Woah, dude! You’re on the news making out with Castiel!” 

“Told you.” Castiel said, triumphantly. 

Dean just laughed and pulled Castiel back in for another deep kiss. 

* * * 

They still had a few issues to iron out before they embarked on a relationship, but in the end those issues seemed like small bumps in the road and it was a smooth ride after that. 

Despite his brother’s relationship with the boss, Sam was treated no differently to anyone else. It was important to Castiel to make it clear that any achievements Sam had were entirely down to Sam himself and he had not been handed anything under family privileges. 

And Sam’s hard work paid off. Within a few years, Novak & Sons had another major overhaul and became Winchester & Novak. (Castiel’s brothers had had something to say about, but as he’d been doing for years until that point, he just ignored them.)

Though, it was only a few months after the changes that Dean asked Castiel how pissed off his brothers would be if it was changed again to Winchester & Winchester. Castiel had just laughed and let Dean place the ring on his finger. 

(Turns out, his brothers were  _ extremely _ pissed off. Oh well.) 

**Author's Note:**

> Also posted on my [tumblr](https://dickspeightjrs.tumblr.com/) as a prompt fill. (Follow me?)
> 
> If you're on tumblr, consider checking out and requesting a prompt from my ['30 Destiel Prompts' challenge.](https://dickspeightjrs.tumblr.com/post/626272747933302784/so-if-you-followed-me-like-4-million-years-ago)
> 
> Comment and give a kudos if you liked?


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